Fall invites us to slow down and savor. The air turns crisp, the trees dress themselves in gold and crimson, and every city seems to glow with a new kind of energy.
We turned to our travel advisors, including staff and esteemed guests, across the country to handpick four cities that capture fall at its very best. Boston, Asheville, Portland, and Chicago emerged as clear winners, each bringing their own flavor of the season, from historic streets framed by fiery leaves to mountain drives and bustling harvest markets.
And with a cozy Sonesta stay waiting at the end of each day, these getaways are as seamless as they are memorable.
đź””Explore All Sonesta Seasonal Offers and Destinations
Table of Contents
1. Boston – New England’s Autumn Classic
Ask the staff at the Royal Sonesta Boston when the city feels at its best, and most of them will say October.
We heard poetic descriptions of the trees flaring red along Charles River against the water and the hint of wood smoke in the air, along with the spirited recommendations of pop-up markets with apple crates and jugs of cider. All in all, there seems to be a clear consensus among our locals: October in Boston is simply magical.
If you’re here during the Head of the Charles Regatta, rowers slice across the river with foliage blazing behind them. On quieter days, the Charles River Esplanade park offers the same rewards: cool air, colors, leaves crunching underfoot, the sense that you’ve walked straight into the best stretch of the year.
Boston Public Garden
Guests often ask where to find the best drive, and we send them west on Route 2. The Mohawk Trail winds through valleys that glow in impossible shades, plush with orange and deep rust this time of year. Some locals like to pull over, cameras forgotten, just to take it in.
Back in the city, fall has its flavors too. You will not want to miss a lobster roll while the season still allows, or a bowl of chowder by the harbor once evenings turn cold.
Even history looks different in autumn. Following the Freedom Trail beneath maples, or stumbling on a harvest market in Copley Square, you see how the old and the new fold together under one canopy of color.
And from the comfort of your hotel room, the view from the Royal Sonesta Boston makes it hard to leave the window. The sun sets over the Charles, washing the water in the same colors you’ve chased all day. Even locals stop and stare.
The Royal Sonesta Boston Hotel
2. Asheville – Blue Ridge Colors and Craft Breweries
If Boston is a postcard, Asheville, NC, is a painting in motion. It’s a picturesque and wallet-friendly getaway.
Fall here announces itself before the leaves turn, as you step outside in the morning and the air has teeth, carrying wood smoke from chimneys hidden in the hills.
Our staff says that’s the real start of the season: when a jacket feels right, the ridges begin to hint at color, and the regulars start to arrive.
The Parkway, a 469-mile drive in the Appalachian Highlands, is still the classic way to see it unfold. Each overlook brings a different blaze of reds and golds, and even longtime locals pull over just to stare.
Over in the Pisgah National Forest, trails feel quieter, the ground softer under pine needles after rain.
The Pisgah National Forest
By the weekend, the city hums with Oktoberfest tents and street fairs, giving the season its own tempo. Ask where to stop for a drink and you’ll hear the same advice: let the beer follow the view. Order a malty pour at Highland or Sierra Nevada with the ridges glowing outside the window, and you’ll understand why locals say Asheville brews autumn right into the glass.
The River Arts District is worth a stop, especially in October. Studios open their doors, paint still drying inside, while downtown fills with music and chatter late into the night. Moving from galleries to bars to patios feels seamless, as if the whole city agreed on the same rhythm.
Back at Americas Best Value Inn Canton, NC, the windows frame the mountains in full color. It’s a cozy, no-frills stop just outside the city. Disconnect from the bustle and connect with nature and each other.
Americas Best Value Inn Canton, NC
3. Portland, Oregon – Forest Trails and Local Flavors
Our team at the Royal Sonesta Portland Downtown will tell you, fall here doesn’t hurry.
Markets brim with apples and squash, weekends bring another round of beer festivals, and the city manages to feel lively without losing its calm. Some of our guests like to hike a ridge in the morning and linger over warm coffee in the afternoon.
The first reds slip in behind the fog.
Washington Park and Forest Park shift week by week, trails softening under maple leaves.
Our staff at the Royal Sonesta Portland Downtown often point guests to the Maple or Wildwood Trails, both close enough to walk from downtown, but quiet enough that you’ll think you’ve left the city. With more time, the Columbia River Gorge pays off the drive: waterfalls framed by canyons of fire-bright color.
When the rain sets in, cider donuts show up on counters, and pumpkin ales pour from the taps. From busy Coffehouse windows, watching gray skies become part of the season’s comfort, a reason to slow down rather than avoid it.
By evening, the Royal Sonesta Portland Downtown pulls you back into the center of it all. Fireplaces glow inside; Washington Park waits with gold still on the trees. It’s the rhythm Portlanders lean on in autumn—bright days outdoors, warmth ready when you return.
The Royal Sonesta Portland Downtown
4. Chicago – Skyscrapers Framed in Gold
Fall changes the Windy city. Golden leaves swirl at the base of the skyline, softening the steel and glass until the towers feel like part of the season themselves.
Walk through Millennium Park or Lincoln Park and you’ll see the trees blazing against the architecture, the lakefront wind carrying the first edge of cold.
From the water, the view shifts again. Autumn light cuts across the skyline in sharp angles, and with summer’s crowds gone, a boat tour feels quieter, almost private. The city seems to glow differently this time of year, its buildings dressed in gold.
Fall in Chicago
Neighborhoods keep their own rhythm. In Lincoln Square, Apple Fest spills over with cider and pastries. Wicker Park markets turn streets into block parties. The film festival fills downtown theaters with late-night conversations. Together they give Chicago its autumn character: a mix of spectacle and familiar warmth.
Our team at The Royal Sonesta Chicago Downtown often points guests toward simple fall rituals such as grabbing coffee for a walk through Grant Park, finding a tucked-away patio while the weather still allows, or just watching the sunset across the river before heading inside.
By the time you return to your room, the season follows you in: color still outside the window, comfort waiting in the quiet.
Lobby at The Royal Sonesta Chicago Downtown
Why We Love Fall Travel At Sonesta
Every city leans into autumn differently, and we try to echo that spirit at Sonesta. Wherever you land, our hotels are meant to keep you close to what makes the season matter.
And because autumn passes quickly, we’ve worked to keep the small details easy. Dinner waiting downstairs when you’d rather stay in, booking that doesn’t add stress, thoughtful touches so you can keep your focus outside, on the leaves, the markets, the moments that make the trip worth taking.
To make the most of your travels:
- Time your trip. In New England, colors crest in mid-October; Asheville’s peaks turn first, with valleys catching up through late October. Portland’s forests glow mid-to-late month, and Chicago’s lakefront tends to peak just before November.
- Book early. Regattas, Oktoberfests, and film festivals can fill hotels fast. Reserving ahead means you get the rooms and views you want.
- Pack smart. Bring layers, shoes you don’t mind wearing all day, and a camera—because even locals stop and stare when the maples turn.
Your Fall Escape Awaits
The leaves turn fast, and by the time November comes, whole valleys and city blocks will already be bare. This year, give yourself the chance to see them while they last.
Some guests plan around festivals, others just want a quiet walk through the parks. Whichever way you prefer, our Sonesta hotels put you close to the colors.
Booking directly with us means the details are handled, so you can spend your time where it matters: outside, watching the season shift.
Find cozy stays for your fall getaway at our:
Disclaimer: The suggested itinerary and points of interest are provided for informational and planning purposes only. Guests are encouraged to independently verify opening hours, availability, travel times, and any potential changes prior to visiting. The inclusion of any businesses, attractions, or destinations does not imply affiliation with or endorsement by Sonesta or its affiliates. Sonesta makes no representations or warranties regarding the accuracy or completeness of the information provided and assumes no responsibility for any inconvenience or loss arising from the use of this information.
